Cyanoacetic acid → Perfluorophenyl 2-cyanoacetate

HRID 1980225Notes

Reaction equation

HRID 1980225 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].C1(N=C=NC2CCCCC2)CCCCC1.[F:22][C:23]1[C:28](O)=[C:27]([F:30])[C:26]([F:31])=[C:25]([F:32])[C:24]=1[F:33]>ClCCl>[F:22][C:23]1[C:28]([O:5][C:4](=[O:6])[CH2:3][C:1]#[N:2])=[C:27]([F:30])[C:26]([F:31])=[C:25]([F:32])[C:24]=1[F:33]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 13041Pentafluorophenol

Product 1

HCID 20402415Perfluorophenyl 2-cyanoacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.25 g. (0.05 moles) of cyanoacetic acid are dissolved in 100 ml. of dichloromethane and a solution of 10.3 g. (0.05 moles) of dicyclohexylcarbodiimide and 9.2 g. (0.05 moles) of pentafluorophenol in 50 ml. of dichloromethane is added. The mixture is stirred at room temperature for 4 hours, cooled to 0° C. and the precipitated dicyclohecylcarbodiimide is removed by filtration, the solvent is removed by distillation and the residue is taken up in petrolether and the precipitated ester is filtered, trituated with petrolether, washed and dried.

Workup

  1. temperaturecooled to 0° C.
  2. customthe precipitated dicyclohecylcarbodiimide is removed by filtration
  3. customthe solvent is removed by distillation
  4. filtrationthe precipitated ester is filtered
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-0256dbc76ddc4550b62a98d4f7e406cb
Source dataset
uspto-grants-1985_04
Patent number
US04508658

Reaction notes

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